IP Library Granted Patent US 12,435,237
Granted Patent B2
US 12,435,237 · App. 17/789,012 · Granted Oct 7, 2025

UV resistant surfacing materials for composite parts

Inventors: Junjie Jeffrey Sang (Newark, DE); Dalip K. Kohli (Churchville, MD)
Assignee: CYTEC INDUSTRIES INC.
C09D163/00C08G59/184C08K7/26C09D7/61C09D7/70
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Quick Facts
Patent No.
US 12,435,237
App. No.
17/789,012
Granted
Oct 7, 2025
Kind
B2
Abstract

A surfacing material that can provide improved UV resistance while providing good surface properties. The surfacing material includes a resin layer formed from a curable resin composition containing: (A) one or more cycloaliphatic epoxy resin(s), each having two or more epoxy groups per molecule; (B) an epoxy-amine adduct having two or more epoxy groups per molecule and obtained by a reaction of (i) an epoxy compound having two or more alicyclic epoxy groups per molecule with (ii) an amine compound having two or more amino groups per molecule; (C) a curing agent and/or a catalyst; (D) ceramic microspheres; and (E) a flow control agent in the form of inorganic particles, which are not ceramic microspheres.

Claims (37)

1. A surfacing material comprising at least one curable resin layer, said curable resin layer comprising:

(A) one or more cycloaliphatic epoxy resin(s), each having two or more epoxy groups per molecule;

(B) an epoxy-amine adduct having two or more epoxy groups per molecule and obtained by a reaction of (i) an epoxy compound having two or more alicyclic epoxy groups per molecule with (ii) an amine compound having two or more amino groups per molecule;

(C) a curing agent and/or a catalyst;

(D) ceramic microspheres; and

(E) a flow control agent in the form of inorganic particles, which are not ceramic microspheres.

2. The surfacing material of claim 1 , wherein the at least one curable resin layer further comprises:

(F) an inorganic pigment selected from metal oxides and carbon black.

3. The surfacing material of claim 1 , wherein the at least one curable resin layer further comprises:

(G) a toughening agent that is not an epoxy-amine adduct and is selected from: thermoplastic polymers, elastic polymers, and core-shell rubber (CSR) particles.

4. The surfacing material according to claim 3 , wherein the toughening agent (G) is selected from: (i) polyvinyl acetal resins (PVB); (ii) polyvinyl formal resins; (iii) a thermoplastic copolymer of polyethersulfone (PES) and polyetherethersulfone (PEES); and (iv) core-shell rubber (CSR) particles.

5. The surfacing material according to claim 1 , wherein the one or more cycloaliphatic epoxy resin(s) is/are represented by the following general Formula I:

where X represents a single bond or a linkage group; the linkage group is selected from: divalent hydrocarbon groups, carbonyl group (—CO—), ether bond (—O—), ester bond (—COO—), amide bond (—CONH—), carbonate bond (—OCOO—), and groups containing two or more of said groups linked to each other.

6. The surfacing material according to claim 5 , wherein the divalent hydrocarbon groups are selected from: straight or branched chain alkylene groups having 1 to 18 carbon atoms, including methylene, methylmethylene, dimethylmethylene, ethylene, propylene, and trimethylene groups; and divalent alicyclic hydrocarbon groups, including 1,2-cyclopentylene, 1,3-cyclopentylene, cyclopentylidene, 1,2-cyclohexylene, 1,3-cyclohexylene, 1,4-cyclo-hexylene, and cyclohexylidene groups.

7. The surfacing material according to claim 1 , wherein the one or more cycloaliphatic epoxy resin(s) is/are selected from polyepoxides having the following chemical structures:

where n is an integer from 1 to 30;

where a, b, c, d, e, f independently denote an integer of 0 to 30.

8. The surfacing material according to claim 1 , wherein the one or more cycloaliphatic epoxy resin(s) is/are selected from polyepoxides having the following chemical structure:

where R represents a group corresponding to a q-valent (q-hydric) alcohol R—(OH)q, except for removing —OH(s) in a number of q there from; p is an integer from 1 to 50; and q is an integer from 1 to 10.

9. The surfacing material according to claim 1 , wherein the one or more cycloaliphatic epoxy resin(s) has/have a viscosity of 2500 mPa·s or less at 25° C., as determined by Brookfield Viscometer.

10. The surfacing material according to claim 1 , wherein the one or more cycloaliphatic epoxy resin(s) is/are selected from: cyclohexanedimethanol diglycidyl ether; cyclohexanediol diglycidyl ether; poly[(2-oxiranyl)-1,2-cyclohexanediol] 2-ethyl-2 (hydroxymethyl)-1,3-propanediol ether; 3′,4′-epoxycyclohexane)methyl 3,4-epoxycyclohexylcarboxylate; 3,4-epoxycyclohexylmethyl-3′,4′-epoxycyclohexanecarboxylate; 3′,4′-epoxycyclohexyl)-3,4-epoxycyclohexane; and hexahydrophthalic acid diglycidylester.

11. The surfacing material according to claim 1 , wherein the epoxy-amine adduct has from 2 to 10 epoxy groups per molecule, and the epoxy groups are positioned at the molecular chain ends of the epoxy-amine adduct.

12. The surfacing material according to claim 1 , wherein the epoxy-amine adduct is represented by Formula II:

where X is, in each occurrence, independently selected from a single bond and a divalent group having at least one atom; R 2 is a divalent organic group having a carbon atom at each bonding site; and n is an integer of 1 or higher.

13. The surfacing material according to claim 1 , wherein the amine compound in the reaction to obtain the epoxy-amine adduct is selected from: polypropylene glycol 130 bis(2-aminopropyl ether; triethyleneglycol diamine; trimethylolpropane polyoxypropylene triamine, and poly(oxy-1,4-butanediyl), alpha-(4-amino-butyl)-omega-(4-aminobutoxy).

14. The surfacing material according to claim 1 , wherein the curing agent and/or catalyst (C) is/are selected from:

(i) amine-containing compound;

(ii) Lewis acid-amine complex;

(iii) acid anhydride; and

(iv) cationic catalyst.

15. The surfacing material according to claim 14 , wherein the curing agent and/or catalyst is a Lewis acid-amine complex selected from: BF 3 ·n-hexylamine, BF 3 ·monoethylamine, BF 3 ·benzylamine, BF 3 ·diethylamine, BF 3 ·piperidine, BF 3 ·triethylamine, BF 3 ·aniline, BF 4 ·n-hexylamine, BF 4 ·monoethylamine, BF 4 ·benzylamine, BF 4 ·diethylamine, BF 4 ·piperidine, BF 4 ·triethylamine, BF 4 ·aniline, PF 5 ·ethylamine, PF 5 ·isopropylamine, PF 5 ·butylamine, PF 5 ·laurylamine, PF 5 ·benzylamine, and AsPF 5 ·laurylamine.

16. The surfacing material according to claim 14 , wherein the curing agent and/or catalyst is an acid anhydride selected from: methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, dodecenylsuccinic anhydride, methyl-endomethylene-tetrahydrophthalic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyl nadic anhydride, carbic anhydride, methylcyclohexenedicarboxylic anhydride, and mixtures thereof.

17. The surfacing material according to claim 16 , wherein the acid anhydride is used in combination with a curing accelerator selected from diazabicycloun-decene, phosphorous compounds, tertiary and quaternary amines.

18. The surfacing material according to claim 14 , wherein the curing agent and/or catalyst is a cationic catalyst selected from: aryldiazonium salts, aryliodonium salts, arylsulfonium salts, and blocked acids.

19. The surfacing material according to claim 1 , wherein the curable resin composition further comprises a curing accelerator selected from: imidazole, dihydrazide, aliphatic polyamine, alkyl and aryl substituted ureas, and bisureas.

20. The surfacing material according to claim 1 , wherein the curable resin composition does not contain any aromatic epoxy resins.

21. The surfacing material according to claim 1 , wherein the flow control agent (E) is selected from: talc, mica, calcium carbonate, alumina, and silica.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 1, 2022
From: SANG, JUNJIE JEFFREY; KOHLI, DALIP K.
To: CYTEC INDUSTRIES INC.
Reel/Frame 060422/0302 →
Continuity (2)
Provisional Application 62954361 · Dec 27, 2019
Related Publication 20230091593A1 · Mar 23, 2023
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